


Worst Scenarios

by Xyopea



Category: Supernatural
Genre: Canon-Typical Violence, Character Death, I guess hosting an angel is suicide, Lucifer's Cage, M/M, Non-Graphic Rape/Non-Con, Non-Graphic Violence, Other, Other Additional Tags to Be Added, Past Rape/Non-con, Prostitute Dean, Sam's full ride scholarship, Suicide
Language: English
Status: In-Progress
Published: 2017-11-21
Updated: 2017-11-25
Packaged: 2019-02-05 04:38:56
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 5,620
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12787122
Author URL: https://archiveofourown.org/users/Xyopea/pseuds/Xyopea
Summary: A series of one-shots describing how things could get worse for our favorite heroes.





	1. One more angel

**Author's Note:**

> Disclaimer: Don't own, don't sue! 
> 
> The rules of association with humans are quite simple and strict. But there are always loopholes.

The rules about association with humans are simple. One is not to interact with them unless it’s part of the Divine Plan. If an angel interacts with a human, the interaction should be minimal, with the best effect for least exposure. Under no circumstances should a Nephilim be born. Simple, easy to follow, no problems here.  
However, after watching humans over the ages, often posing as one, certain behaviors stick. Sexuality is a good example. Angels are generally genderless, sexless. But once an angel took a human vessel, certain parts of the anatomy became available, both for exploration and fornication. The easy pleasure can become addictive. Gabriel is an example of an archangel (imagine that, one of the First, the Messenger himself) who sampled the forbidden pleasures of the flesh- and chose to vanish before proper measures could be applied.  
Since the punishment for unneeded interaction is Falling or death, but the forbidden fruit is the sweetest, some angels used their intelligence and wisdom to search for loopholes. And one presented itself in a form of a desperate prayer.  
“I don’t even know if you exist, but if you do, please… Dad’s been gone for too long, and we’re out of money… I failed to steal food today, got kicked out of the bar… I know that I’m a sinner, but why does Sammy have to suffer?”  
Dean Winchester, the Sword of Michael. God has plans for this one, and he’s willing to do anything to provide for his brother, who is also meant to survive until he’s ready to break the Seals and serve Lucifer as his vessel during the Apocalypse. Having those two die just won’t do. They are also to remain together, to maintain their bond as brothers until their time comes. Perfect.  
***  
Dean watched the gas station from his position under a tree. Luckily it wasn’t raining that night. It was growing late, and soon the flow of the cars will slow down enough to provide a window of opportunity. Then to point a gun at the poor worker and hope not to get arrested.  
A hand placed on his shoulder made him spin and reach for the gun.  
“Easy there, boy. I mean no harm.”  
The man who managed to sneak up on the teenager (how did he do that?) wore an expensive suit, and was smiling in the creepiest way Dean could imagine, and that was impressive, considering the amount of evil beings he had part in killing.  
“What do you want?”  
“You look like you could use a warm dinner.”  
“I asked what do you want, not what I look like.”  
“Was just offering to do you a favor.” The voice was even sleazier than the smile.  
Dean wasn’t born yesterday, he’d heard of the type. Predators, perverts… Rich guys who think they can have anything they want. And by anything, Winchester could name quite a few things.  
“Yeah, right. In exchange for waking up in a bath of ice with body parts missing or not waking up at all?”  
The stranger stopped smiling. It could have something to do with the boy reaching into his jacket for a poorly concealed gun.  
“50 bucks. Sex. Simple as that.”  
It sounded simple. And had higher odds of coming back to Sammy… what’s one more disgusting thing compared to what he had to do as a Hunter?  
And when Dean looked at the sleaze-ball, grass-green turned to hard emeralds, and the sneer turned into a mockery of the smile offered to prettiest classmates.  
“Care to double the offer?”  
***  
Over a decade later  
“You’re not going to die a virgin.” The hunter looked at the angel with determination.  
Castiel smiled at Dean sadly.  
“That’s not how I imagined you’d offer. But I don’t mind…”  
“Wow, wait a moment. Who said anything about me? I thought we’d set you with a nice girl from the club down the block! And what do you mean imagined? The fuck, Cas?”  
“Why not? You didn’t mind the others!”  
“What others? What are you talking about?”  
The angel looked puzzled at Dean’s sudden anger.  
“The others you’ve bedded. Or is an exchange of money a necessary requirement?”  
“Did you just call me a whore?”  
“Your generosity with your body is well known in Heaven. Many of the Host were saved from temptation and Falling by the means of procured affection from you. I don’t see any cause for shame or anger, for exchanging money for favor is a wide known practice through the ages.”  
Dean sat down on the shaky motel bed and took a deep breath.  
“Castiel, Angel of God, are you telling me now that those bastards, who didn’t think twice about fucking a teenager, were of the Host? And considered themselves doing a good thing?”  
“From what I’ve gathered, you prayed for a way to provide for your brother. It was sent to you.”  
“And the sex?”  
“Carnal temptation is hard to overcome, and approaching a human without a divine reason, such as providing for a chosen, is forbidden. But all sides got what they wanted, so why are you so upset?”  
“You really don’t see the problem, do you? And after what you’ve done to me, you’re after Sam’s body too, just in a different way. Well let’s see. Angel infestation is by bloodlines, is it?”  
And emeralds turned to blazing stars, and the smile turned feral.  
“Dean, what are you…”  
“Lucifer, if you can hear me, if you feel like screwing a divine plan, to you my body and soul I trust. If you agree to spare Sammy, I’m in.”  
The walls shook and the lights flashed as the presence of an archangel grew near. Castiel looked with terror as Dean stood up and spread his arms.  
“After all, what’s one more angel inside me?”  
Lucifer embraced the aching soul, sampled its sorrow and found it sweeter than Nicks. And as he obliterated his first angel, he felt the vessel rejoice.


	2. Useless emotion

**Summary for the Chapter:**

> All things considered, love just isn't worth the effort...

**Notes for the Chapter:**

> Warnings here: violence, sex- none of them graphic.

During his life, Dean has learned that love is a tiring, unneeded thing. First he had to love Sam. That he didn’t mind. Sure, the boy was somewhat heavy to carry as a kid, but he grew up nicely and sometimes was fun to talk to. But the order was clear- to protect Sam or to shoot him. With the trouble the kid attracted, why grow attached?  
  
Loving his father was even harder. After all the times the brothers were dumped at Bobby’s or in a cheap motel, or even in a shack in the middle of nowhere, he decided that love was too much, so he stuck with obedience and duty. But not love. When John signed the demon deal in exchange for Dean’s life, the young man felt gratitude, but not love.  
  
Bobby. Good old Bobby. Never saying a word when John got drunk, stepping in only when the beatings were too harsh. He murdered his own wife, for fucking out loud, why should he love a skinny, clumsy kid, especially the dumber of the two. He taught Dean to tinker, took him fishing with Sammy. But that was all for Sammy. Dean knew there was no love there.  
  
The girls, the women, the occasional men. Warmth for the night. Sometimes money. When that chick in high school told Dean he was just an unloved, abandoned kid, she had no idea how right she was. They all could find another body for the next night. Some went back to their spouses after a quick shower. One didn’t have to be as smart as Sam was to know that sex doesn’t equal love.  
  
Then there was Hell, and Alastair. He bargained with Lilith to get Dean’s soul. He gave him decades of undivided attention. Never too busy. Not a single word untrue. Skilled. Stronger. He didn’t demand, only offered. He didn’t deny- only provided, even if all he provided was agony. Best of all, he never spoke of love. And one day, when Alastair propped his head up with the handle of a knife and made his offer, Dean lowered his face and kissed the hand that held the knife, and said “yes”.  
  
If he felt special before, it was nothing compared to what he’d got. Alastair taught him to cut, to share the agony. And in the nights, he took Dean deeper into Hell, wrapped him in sheer sin and filled the cracks of his soul with his own darkness.  
  
10 years later, Castiel broke through Hell’s gates, battled countless guards, desperate to reach the Righteous Man in time, only to find two white eyed demons embraced, armed and furious. The light he mistook for the shine of a Righteous soul was from the endless admiration and devotion that the newly shaped torturer felt for his master.  
  
“Dean Winchester! I’m here to raise you…” He still said.  
  
The torturer that was once a hunter approached the Angel with the sweetest smile. Alastair remained on his spot, observing with interest.  
  
“Why are you here?” He asked as he rubbed bodily against the shining entity, graceful, seductive, just the way a proper demon should behave.  
  
“Because God loves you and needs you back on Earth.”  
  
“Love? I remember love. I even remember loving…” Dean purred, eyes turning to green for a moment, then white again, as he struck Castiel with his own angel blade. “And what a worthless thing it was.”  
  
And Alastair felt pride. But not love. Because seriously, what a useless emotion.


	3. A service pet

**Summary for the Chapter:**

> Would it really damage some eternal plan if Fergus got himself a Winchester of his own?

**Notes for the Chapter:**

> Warnings: pain (non-graphic), nudity (not graphic), some misplaced affection.

When Sam Winchester got his soul back from the Cage, Crowley started thinking. On one side, he saw the madness it triggered. On the other hand, it would be a crying shame not to do some good in his own way. After all, the angels had two Winchesters. Was it so wrong to want one for poor little Fergus, as a reward for his perfectly good intentions?  
So he had his demons research a spell, gathered the ingredients, and cast the spell, only to end up with an armful of a sobbing, terrified mess.  
On one side, that was to be expected. On the other hand, he expected a Winchester, not a ragdoll. Then again, Crowley could recall several instances where Alastair’s pet projects behaved the same. But some recovered. And went hunting the next day, if the rumors served him well. Well, it wouldn’t really hurt to try. So he approached the shivering human, and brushed his matted hair from his face, and spoke as softly as he never did to his own son.  
  
“Easy, Adam. Shhh, you’re safe now!”  
The use of the name seemed to work, and a pair of eyes red with tears met Crowley’s own.  
“A…Adam.” The boy rasped.  
“Yes. You’re Adam. And I’m Crowley.”  
“Crowley.” The name was accompanied with a nod of comprehension. There they were, the Winchester genes - a mind more or less sound after something beyond horror. “D… dog?”  
It took the demon a second to comprehend that Adam was probably close enough to death to see Juliet. And compared to two pissed-off archangels, she could indeed appear harmless enough. Service hellhounds sounded like Crowley’s idea of a good irony.  
“Yes, and she’s a good dog, nice and warm! Want to pet her?”  
Milligan tried to stand and failed. Immediately he cowered down, expecting punishment.  
“Easy, dear. You’ve been through a terrible experience. The Cage is behind you. It’s only Hell out here. Juliet, heel!”  
The hellhound bounded closer and sat calmly still while her master allowed a complete stranger to rub her head.  
“Now let’s get you cleaned. I swear, that blasted Castiel had a point when he said that some insects are more useful than angels.”  
Adam just nodded in agreement into his rescuers’ jacket. He was safe, and warm, and didn’t hurt. And if he smelled of sulfur, well, at least he didn’t smell like… the human forced himself not to think about the Cage and focused on Crowley and Juliet and the good place he was at.  
  
***  
  
Few days later, Adam heard familiar footsteps and raised his head to smile at the great King of Hell with utter adoration. Juliet made a displeased sound, when her cuddle toy shifted from curled position to a kneeling one.  
“Adam, my boy. How are you?”  
“Much better, thanks to you, Your Majesty.” After all that Crowley has done for him, the healing, the safe place to stay, basic manners and gratitude were the least Milligan could offer. “How can I serve you?”  
“I was wondering. Word has it that you studied medicine before your… untimely demise.”  
“I wanted to become a surgeon.” Could it be, will he actually be allowed to complete his studies somehow? Be of use to this great demon?  
“Ah, the fine art of cutting the flesh properly.” Crowley ran his fingers through Adams’ hair, enjoying the clean, soft feeling. “So underappreciated. Have you started the practical classes?”  
“Only basic morgue dissection.”  
“Well, we’re all somewhat dead here, so I guess it won’t be a problem.” And did the King actually laugh? “What would you say if I offered to teach you a different kind of cutting? Give you a job where many failed, including your no-good idiot of a brother.”  
Adam sneered at the mention of Sam and Dean. Crowley already explained to him that all those terrible things happened only because he was related to the denim-clad losers and their drunk of a father. He was tainted with that foul blood. How did he get so lucky to gain the attention and aid of this powerful being, to be appreciated despite it? And now he could best them at something, and please the great King at the same time. Could afterlife get any better?  
“Anything for you” Was the only possible reply, accented with an admiring look.  
“That’s the spirit! Now come here. I’ll show you your new workplace and teach you the ropes, so to speak.”  
***  
When Bobby ended up in Hell, he expected the worst. The boys haven’t told him the details, but seeing the age-old looks in their eyes and hearing their screams at night was enough.  
The door to his cell opened and he braced himself, but instead of hell-knows-what, he saw the familiar suit-clad figure.  
“Robert! How delightful to see you again!”  
“Crowley. I wish I could say the same.”  
“And here I thought you’d be glad to see a familiar face.”  
“In different circumstances- maybe.”  
“I see my company isn’t good enough for you. That’s fine by me. I brought another familiar face to entertain you. I hope you remember him. Adam!”  
The young man that entered the cell was as naked as his biblical namesake, his only cover being the blond hair that flowed to his waist. He had a look of utter contempt on his face, strongly reminding of the one the Winchesters saved for angels and high demons. Despite everything, Bobby could see the familial semblance between him and John.  
“Milligan? Balls! What has that bastard done to you?”  
“Much less than what you and your friends did.” Adam replied. “But that’s fine. Should my King permit, I’ll even the score.”  
“Permission granted. If you need anything, you know where to find me.” Crowley pulled a whip out of thin air and gave it to his own, perfect Winchester.  
 


	4. A gift from a brother

**Summary for the Chapter:**

> Gabriel really wants to do something nice for Castiel. As usual, it doesn't matter who gets hurt in the process.

**Notes for the Chapter:**

> Warning: Non-Con (not graphic)

It started during the adventure in TV land. One of the channels was a pay-per-view-porn, and luckily Sam wasn’t in that one… but Cas was. Dean recognized the type of the movie- the one where a “virgin” or an “inexperienced str8” gets roughly introduced to gay sex, starring the winged wonder in the role of the abovementioned virgin. He acted out of mercy, asking for consent in a whisper into the angel’s ear. He got it too, along with an trusting gaze from those blue eyes and a small gasp from that perfect mouth. Dean was ladies-only-kinsey-1 kind of a guy, but Castiel was so willing and curious, so helpless, and there were other men around him, offering to take over if Dean would just back off, all of them huge and hairy, weapons primed and ready. So he acted his part, and did everything he loved experiencing and all that he heard about that was supposed to feel good, tasting and cuddling and taking long time to prepare, leaving the angel boneless and purring and spent. Cas was overjoyed, kept saying something about it being an eye-opening experience and how he never knew a body could feel so good. Dean on the other hand wanted to die. He felt dirty, ashamed, and sick. But he put on his best fake smile for the angel and just held him close.  
Eventually they managed to beat the accursed archangel, and return to reality. Dean never wanted to kill anyone that much. Seriously. Not even Alastair. Because it seems that demons have principles that archangels don’t.  
  
Later Sam told Dean that he spent that time window with two frisky girls, one of which, Genevieve or something, reminded him of Rubi and was dressed like a demon, which was hilarious really. Dean replied that he didn’t feel comfortable talking about this with his baby brother and later scrubbed himself bloody in the shower.  
  
Castiel didn’t seem to notice. He dove into the newly discovered possibilities with a passion. Dean did him a favor and taught him some pick-up techniques, then spent the evening throwing up. The angel didn’t notice and put his vessel to a nightly use, only to return by morning looking somewhat puzzled and nervous. Nothing felt quite right, and he couldn’t point out why. When he tried to question the older Winchester about it, he got a yelling in return, which hurt more than it was probably meant to. Still, he kept on helping the brothers in their attempt to avoid becoming ‘angelic prom-gowns’, while feeling that something major was missing from his life.  
That’s where Gabriel ran out of patience and decided to kill two, or even three birds with one stone. One night he showed up and had a very productive chat with Dean. The next evening Winchester rented two motel rooms instead of one, asked Sam to sleep in the spare one and invited Castiel to sleep by his side, instead of standing watch or looking for a pick-up. And when the angel slipped under the blanket, he discovered that Dean wore nothing under it and was quite pleasant to touch.  
He didn’t notice that Dean took longer to shower the next morning, nor that Baby’s gas tank was full and there was an accidental mix-up of pizza orders (who on Earth orders pizza at 8 am?) which spared the brothers the expenses on breakfast due to free delivery.  
The next night the arrangement remained, so did the next ones, and Sam actually congratulated Castiel and Dean on figuring things out between them. He didn’t notice that Dean lost weight. But Gabriel did. And Sam had an accident that morning, slipping in the shower and almost cracking his head open. Threat made clear, the Trickster waited until Cas went away to scout for information and had a sterner talk with the hunter. Dean started eating better after it.  
  
Along came Zachariah. After seeing that threatening Sam does little to break Deans’ defiance, he went for the low-hanging fruit.  
“Come on, think about it. You let Michael in, and you’ll be too high ranking for Castiel to ever touch you again. Would that be so bad?”  
The look on his face must’ve been quite informative, because Sam actually asked:  
“Why would Dean want to be away from the man he loves?”  
That got both Zachariah and the older Winchester laughing, one honestly and the other hysterically.  
“Sammy, Sammy, you really have no idea, do you?” The angel recovered first. “You tell him or should I?”  
“Help yourself.” Dean replied.  
“As you wish. See, Dean here doesn’t love boys that way. He’s so straight they should put his photo by the definition at the dictionary.”  
“But Cas…”  
“Castiel is naïve, mistaking forced affection for real one.”  
“Then why?” Sam just couldn’t put the pieces together.  
“If I say his name, try to kill myself or refuse Cas- you die. Or Bobby, or Lisa, or anyone else I care about. Mom and dad will end up dragged from Heaven to Hell. He said he can make it all happen. But if I’m good, if I act like a porn slut, if Cas is happy, then we’ll never have to worry about gas, or food. Did you even notice how quickly our injuries healed after the last few fights? And now I have another archangel after my ass, and another after yours. And forget Lucifer, I doubt he can be worse than the one who did this to me. Ever since TV land…”  
Zachariah nodded in understanding.  
“Gabriel is alive, then. And his sense of humor is intact. But he’s no match for Michael or Lucifer. Let them in, boys. Become stronger. End the pain.”  
Sam looked absolutely sick. All this time Dean was suffering and he saw nothing. Said nothing.  
“Don’t blame yourself, Sammy. Your brother did a remarkable job of keeping you in the dark.”  
“Brother in the dark… You know what? Let’s do this. Sign me up.” Dean suddenly smiled.  
“You mean it? You’ll say yes?” Zachariah actually knelt to face Dean, wiped the blood from his lips. “Would you do it now?”  
“As long as I get a few quick answers. Some humans might survive if I say yes?”  
“Most likely. About a third or so.”  
“And only a Winchester can contain Michael or Lucifer, the strongest archangels, stronger than Gabriel.”  
“Only you. Sons of John Winchester.”  
“Awesome. Well, in this case… Lucifer, to you my soul and body I trust.”  
“What?” All present stared at Dean as he stood up and spread his arms.  
“I say yes if you promise to spare my brother.”  
And the walls shook with the presence of an approaching archangel. And later, when Lucifer ended the existence of his treacherous sibling, he let green flash in his eyes and said:  
“Consider this a gift from one brother to another.”


	5. We can even remove one rule

**Summary for the Chapter:**

> Oh, please! It's not like Hell has anything Dean haven't seen yet. Or anyone.

**Notes for the Chapter:**

> Another take on Dean in Hell, from a slightly different angle. 
> 
> Warnings: violence, sex, all non-graphic

I don’t know if anyone told you, but silver bullets don’t grow on trees. Also, unsurprisingly, some priests that will only bless a weapon or give you Holy Water if you pay them. And teenagers eat double their weight, and that’s before they hit a growth spurt. The abovementioned teenagers also grow out of clothes faster than you can buy them. And they also have an annoying preferance for healthy nutrition, which, again unsurprisingly, is quite expensive. Unfortunately credit card frauds will only get you so much. So, that’s how Dean ended up first on street corners, then, when his pain endurance became known, in exclusive clubs.

Every time John took off hunting hell-knows- what (sometimes literally), and took his precious time, or went to Windom, Minnesota (what the fuck was wrong with this town? Whatever it was, John spent there at least a couple of months every year), Dean only had to post a certain message in certain magazines or internet forums. No more than a couple of hours later, he would pack Sam up and move to a nicer hotel, only returning to the dumps when John called that he’ll be returning soon. There he lavished attention on the client, and after that, he could afford to spoil Sam with some delicacy or a trip to a concert, or a rare book.

There were if fact only 3 items on Deans’ “no” list. No permanent damage of any sort. No touching Sammy. Baby brother may be present for extra charge, but only to act the part of a voyeur or a terrified observer. And no conversion- Dean knew well that some of his clients were Reapers, vampires, other exotic beings, but Dean was to remain human at the end of the session.

After almost getting caught, Dean learned to hide his own credit cards in Sam’s bag, knowing well John would never look there. He actually dragged his precious little brother to a street clinic once, to learn some improved patching techniques. John actually caught wind of that one, and actually had a word of approval for his smart son (not the one who arranged it, mind you). And Dean prospered, at least as much as being a pain-specializing escort could be. As he grew older, his prices went up, since his endurance improved and there was no longer the risk of some school do-good finding out. By that time, Sam knew exactly what his “full-ride scholarship” was all about. Hell, it took some high acting to prevent their so-called dad from figuring out his sons planned it all from the start. When the youngest Winchester left for school, his bag held the latest laptop, some really fancy clothes for parties and a key to a bank deposit box with some jewelry meant to be traded for spending cash.

But then John had to start the whole Colt business. Dean actually ended up with damage he couldn’t withstand. Luckily, the Reaper was an old client, and really didn’t mind holding off until John made one of the rare selfless decisions in his life. Later, as those Hellhounds tore him to bits, he was more worried about leaving Sam with Lilith in the same room than about Hell itself. So when Alastair approached him, brandishing a blade, Dean just smiled at him:   
“Don’t you think that this is a bit too much of an effort, if all you wanted was a longer session?”  
And the torturer actually laughed at being recognized even in his true form.   
“But won’t I get a kiss for the effort?” He teased. "Besides, what would people really think if we didn't follow protocol?"  
“You know well that I'd do anything for my best-paying client. Besides, now we have all the time in the world.” 

And when the Host went through Hell’s gates to save the Righteous Man, instead of a tormented soul, all they found was a couple of old-time lovers, who just happened to need a terrified observer for their games. And since Cas wasn’t Sammy, there was no rule against including him.


	6. Leave that part...

**Summary for the Chapter:**

> Crowley follows every deal to the letter. And Bobby has a line of his deal left.

**Notes for the Chapter:**

> Warnings: violence, death (not graphic)

Crowley took real delight in angering beings of all kinds and getting away with it. In different circumstances, he could’ve made a great Trickster. Making wishes come true- check. Causing well deserved sorrow- check. Still, being a crossroads demon still had its advantages. And he was about to demonstrate one to his demon servants, cementing further his status as the King of Hell while he was at it.  


So when the heads of departments gathered in his throne chamber, they expected another speech, perhaps a public execution or two, but not to see Crowley standing next to his throne, with something or someone placed on it, covered with a not too clean rag. The covered figure seemed to move, in apparent struggle, if the erratic pattern of it seemed like an indicator. Also, Juliet the Hellhound was sitting by her master’s side, clearly there to assist. So whoever was bound to the throne had to be an impressive foe. The crowd started whispering. Could it be? Was it one of the denim-clad terrors? Did the showoff soul merchant manage a feat so great? But if so, when the supposed Winchester will rise from death again, won’t it be hell to pay, literally?  
Crowley listened to the whispers with delight, savoring the fear and respect. He allowed the volume to rise, for the conversations to turn from whispers to almost shouts, before clapping his hands twice, to get the attention he clearly deserved.  


“Greetings. I’d say Ladies and Gentlemen, but really, we all know who you are.” He started his speech. “As some of you guessed correctly, I’ve brought you here to present my latest acquisition, one you might find impressive. Any guesses to what’s behind door number 1?”  


A female demon stepped forward, feeling brave.  


“Is that a Winchester, sir?”  
The sound of the name made the covered person still his struggles for a moment, before returning to them with new fervor. The demoness squealed in delight.  
“Almost.” Crowley drawled. “Better.”  
“What can possibly be better than besting the famous hunters?” Another demon, a male one, dared to ask.  
“Famous hunters, yes. The weapons of mass distraction from divine plans. But all weapons must be honed. And all greatest heroes are nurtured. And I’m not talking about the guy who lasted a century and left Alastair in the dust.”  


The reminder of the great torturer and John Winchester’s resilience caused a new wave of murmurs in the crowd.  
“Now, is there anyone of the older crowd present, who can remind me of another hunter, perhaps, one who killed his first demon without any previous knowledge, celestial aid or Azazel’s gifts? One who hunted monsters and demons alike long before Dean learned what breasts are really for? One who gave us trouble for decades, teaching young hunters, helping them escape the human law and our own justice?”  
“You really got him? After all those years? Soul yours and all that?” An older demon pushed forward.  
“Whom, sir?” A young demon asked. “Who can be scarier than a man of the Winchester clan?”  
The older demon approached the covered prisoner.  
“He sure deserves to be presented on the throne. May I, my King?” His hands actually shook with expectation.  
“Go ahead. I’m not touching that rag. Juliet dragged it from his own salvage yard, clever girl that she is.” Crowley waved his hand in a gesture of regal permission. “Demons and demons, where you expected to see a mere limb, I present you the heart and mind of the American hunters. Robert Singer, felled by a line in a contract he himself sealed with a kiss. Keep the part about his legs, he said. Thought he’d got the best of me. Just happened to forget that I’m Crowley, I never lose.”  


The demon pulled the cover off. And with the rag removed, Bobby finally able to see the black, yellow and even white eyes of those who gathered to see his fall. The higher the demon ranked, the more it cheered, and the louder it applauded. And above all, Crowley’s red eyes stood out, as he reveled in the attention and victory.  
“You have no idea how many of us have longed to see you here.” The King of Hell spoke to his prisoner.  
“Good. Now I have a kill list.” Singer wasn’t about to show fear.  
“Now you can see who Dean got his manners from. Who Sam got his research skills and smarts from. A couple of days every couple of months, occasionally, but still enough to shape up our greatest opponents. Got anything else to say?” Crowley gloated.  
“I think I’ll just sit here on your highly cozy throne and listen to you praise my boys. Don’t let me stop you.” The old hunter actually smiled back before trying to lung forward and break loose again. The chains that held him clinked almost cheerfully as he failed again and remained seating.  
“So, what say you, what shall become of this man? Should he be just left in a cell somewhere for us to forget?”  
“No!” Someone called from the crowd.  
“Perhaps a cage here, in the throne room, for demons and guests alike to watch and admire?”  
This suggestion brought murmurs of approval.  
“Sir, if I may?” The female demon who took the first guess decided to try her luck again.  
“I’m all ears, dear.”  
“The Winchesters don’t know he’s here, right? There won’t be a celestial rescue?”  
“Nope. He’s here for a proper eternity.”  
“Then, how about making him one of us? Sure, it will take time, but the sweet irony…”  


Bobby paled at the suggestion. To become the very thing he fought so hard against, to turn on the people he cared for. The very thought was beyond terrifying.  
“Now that’s the spirit I expect from my finest servants. And just for that, you can even have the first go on him, before I take over this very important project. After all, Robert dear, I torture all of my friends.”  
The roar of blood in Bobby’s ears as panic overtook him wasn’t enough to silence the roar of approval from the demonic crowd.  
***  


Bobby entered the motel room quietly, picking the lock with practiced ease. The salt barrier was blown off by a hellhound earlier. How could his precious boys be so careless? He taught them better. Silently he approached the sleeping figures. Sam, tossing and turning, and Dean, deep in a nightmare, which was quite merciful compared to his usual night terrors. As good as his, those children had grown into fine men. Feared by Hell, respected by Heaven. So tired, so battle weary. Bobby placed a small charm on each of the boys’ pillows, enchanted to give them the sweetest dreams. And just like that, their frowns vanished, their breath evened. Finally resting, after more than two decades on the run, in war, literally in Hell.  
He watched them sleep for a while, until he heard Juliet whine outside. Then he took the demon knife from under Sam’s pillow, covered his mouth, and slit his throat with a fast, practiced move. A mercy kill, a silent one. Still, Dean shifted in his bed, cracked his eyes just a bit, and smiled, still somewhat captured in a dream.  


“Unca’ Bobby?” He asked, confused by the scent of blood in the air.  


A single shot sent him back to rest, this time not to be interrupted.

**Notes for the Chapter:**

> Feedback or a challenge will be appreciated.


End file.
